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$101+ Cheap flights from Chicago (CHI) to Winnipeg (YWG)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Nov 5 — Nov 121
Tue 11/5
Tue 11/12
1 adult, Economy
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Cheap flight deals from Chicago to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 31, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

April

Cheapest in

March

Round-trip from

$282
(Kiwi.com)

One-way from

$101
(Kiwi.com)
Provider with most accurate pricing for Chicago (CHI)-Winnipeg flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Winnipeg flights.
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High demand for flights, 27% potential price rise
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Best time to find cheap flights, 60% potential price drop
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From Chicago (CHI) to Winnipeg
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One-way flight from Chicago (CHI) to Winnipeg
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Find flight deals from Chicago to Winnipeg

Cheapest flights from Chicago to Winnipeg
Explore the most affordable flight options available from Chicago to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 31, 2024.

This Mytrip deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/76:33 pmORD - YWG
2 stops20h 37mMultiple Airlines
Tue 12/106:20 amYWG - ORD
3 stops23h 10mMultiple Airlines
Deal found 10/31$328
This Mytrip deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/712:55 pmMDW - YWG
2 stops8h 14mMultiple Airlines
Tue 12/106:45 pmYWG - MDW
2 stops23h 47mMultiple Airlines
Deal found 10/30$482
This United Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/710:35 amORD - YWG
2 stops12h 48mUnited Airlines
Tue 12/102:15 pmYWG - ORD
Nonstop2h 30mUnited Airlines
Deal found 10/30$492
This Air Canada deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/87:19 amORD - YWG
1 stop6h 39mAir Canada
Sun 12/1512:15 pmYWG - ORD
1 stop7h 17mAir Canada
Deal found 10/30$499
This Gotogate deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2911:15 amMDW - YWG
2 stops9h 54mPorter Airlines
Sun 12/16:45 pmYWG - MDW
1 stop21h 55mPorter Airlines
Deal found 10/30$504
This Kissandfly.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2912:52 pmORD - YWG
Nonstop2h 36mLufthansa
Sun 12/12:15 pmYWG - ORD
Nonstop2h 30mLufthansa
Deal found 10/30$507
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/145:25 pmORD - YWG
1 stop6h 09mDelta
Fri 1/106:40 amYWG - ORD
2 stops6h 34mDelta
Deal found 10/31$519
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/77:14 pmMDW - YWG
1 stop4h 20mDelta
Tue 12/1012:35 pmYWG - MDW
1 stop5h 57mDelta
Deal found 10/30$534
This FlightHub deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/99:50 amORD - YWG
1 stop13h 44mWestJet
Thu 1/28:00 pmYWG - ORD
2 stops22h 48mWestJet
Deal found 10/30$591
This SmartFares deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/297:17 pmMDW - YWG
1 stop4h 10mWestJet
Fri 12/66:00 amYWG - MDW
2 stops12h 32mWestJet
Deal found 10/30$639
This Aeromexico deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/121:05 amORD - YWG
2 stops34h 21mAeromexico
Thu 11/148:00 pmYWG - ORD
2 stops27h 14mAeromexico
Deal found 10/30$2,258

Find flights from Chicago to Winnipeg within your budget

Customize your flight search to find flights from Chicago to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,570,725 searches. Data last updated October 31, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 12/5

5:59 pm-3:10 pm

1 stop21h 11m

$101

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 12/5

12:52 pm-3:28 pm

Nonstop2h 36m

$213

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 12/15

12:52 pm-3:28 pm

Nonstop2h 36m

$231

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 12/15

7:14 pm-11:34 pm

1 stop4h 20m

$240

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 2/28

12:30 pm-12:34 am

2 stops12h 04m

$274

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 12/15

5:35 pm-6:04 pm

2 stops24h 29m

$314

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 12/5

12:43 pm-12:36 am

1 stop11h 53m

$229

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 12/30

11:48 am-11:52 am

1 stop24h 04m

$303

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 11/22

1:35 pm-11:27 pm

2 stops9h 52m

$383

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 12/4

1:00 am-11:25 am

2 stops34h 25m

$1,119

Flights are sorted by cheapest first

Deals found on 10/30

Showing 1-10 of 21 results
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Compare providers for flights from Chicago to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Winnipeg in October.
ProviderPrice AccuracyTrust Score*Cancellation Policy
ExpediaPrice Accuracy1 starTrust Score*3 starsCancellation PolicyAirline Policy
eDreamsPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy
FlightHubPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Chicago to Winnipeg

Get recent, data-driven insights about flights from Chicago to Winnipeg including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Chicago to Winnipeg?

Currently, September is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $337). Flying from Chicago to Winnipeg in February is currently the most expensive (average of $513). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to YWG?

Find hourly flight availability from Chicago to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 31, 2024.

One of the essential ways to save on airfare from Chicago to Winnipeg is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 19% on airfare.

What is the cheapest day to fly from Chicago to Winnipeg?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Winnipeg. Price data was last updated on October 27, 2024.

Travelers seeking maximum savings on their Chicago to Winnipeg flight should consider departing on Saturday mornings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Find deals

Rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Winnipeg ranges from 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.

Temperature in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated October 31, 2024.
See what other customers who have flown with Delta, Air Canada and Aeromexico from Chicago to Winnipeg have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,835 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta
8.0
Very good
8,835 reviews
Delta
8.0
Very good
8,835 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Porter Airlines
7.8
Good
294 reviews
Delta
8.0
Very good
8,835 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Aeromexico
7.5
Good
2,032 reviews
Delta
8.0
Very good
8,835 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

United Airlines
7.4
Good
9,240 reviews
Delta
8.0
Very good
8,835 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

WestJet
7.3
Good
2,804 reviews
Delta
8.0
Very good
8,835 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Winnipeg from Chicago?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Chicago. On average, Winnipeg has 1 inbound flight from Chicago per day from 3 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • Can I find flights from Chicago to Winnipeg for under $300 on Cheapflights?

    Yes, there are multiple flights from Chicago to Winnipeg for under $300. The cheapest flight booked recently is on Multiple Airlines for just $282, but on average you can expect to pay $642.

  • Are there nonstop flights from Chicago to Winnipeg for under $600 on Cheapflights?

    Cheapflights has at least 3 direct flights from Chicago to Winnipeg under $600. A good price for a nonstop flight from Chicago to Winnipeg is less than $532.

  • Are there last-minute flights available from Chicago to Winnipeg for under $600?

    There are currently 10+ open flights from Chicago to Winnipeg within the next 7 days for less than $600.

  • What are the cheapest airlines flying from Chicago to Winnipeg round-trip?

    Flying on United Airlines is currently your cheapest option to Winnipeg, with prices starting at $492. Additional round-trip tickets that might be worth considering are offered by Air Canada and Porter Airlines, with the lowest prices starting at $499 and $504, respectively. These flights start at 7% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Winnipeg one-way?

    One-way options have recently been found by users for as low as $213 on Air Canada. Other airlines that offer cheap prices include United Airlines from $231 and Delta from $240 one-way.

  • What are the most reliable airlines from Chicago to Winnipeg?

    The top 3 most reliable airlines when flying from Chicago to Winnipeg are SkyWest Airlines (85%), Air Canada (85%) and United Airlines (85%).

  • What are the cheapest flights from Chicago to Winnipeg?

    The cheapest flight price from Chicago to Winnipeg is $250. On average you can expect to pay $625. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $224.

  • What does ORD to YWG mean?

    Chicago O'Hare Intl Airport is ORD and Winnipeg Airport is YWG. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Ready for more IATA code knowledge? These are related airports for your current travel destination: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Chicago to Winnipeg that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Winnipeg flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Winnipeg with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Winnipeg flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Chicago to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Chicago to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Winnipeg.

  • Can I find deals for business class flights from Chicago to Winnipeg?

    Yes. Cheapflights offers flight deals from Chicago to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Chicago to Winnipeg that allow pets onboard?

    Many airlines flying from Chicago to Winnipeg offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Winnipeg?

    Yes, you can often find last-minute deals on Chicago to Winnipeg flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Winnipeg flight deals updated?

    The Chicago to Winnipeg flight deals you see on this page were last updated on 10/31.

  • What is the cheapest month to book a flight from Chicago to Winnipeg?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $337). Flying from Chicago to Winnipeg in February is currently the most expensive (average of $513). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Chicago to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Winnipeg flights
Midway to Winnipeg flights
St. Louis to Winnipeg flights

Top 3 airlines flying from Chicago to Winnipeg

Discover the top 3 airlines that operate flights from Chicago to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,570,725 searches. Data last updated October 31, 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$255Average$578FlexibilityNo cancel feeOn-time67%
DeltaCheapest$462Average$618FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$535Average$724FlexibilityNo cancel feeOn-time69%
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